2- Hydroxyethylamine

Reaction of cyanohydrins with absolute ethanol in the presence of HCl yields the ethyl esters of a-hydroxy acids (3). A/-substituted amides can be synthesized by heating a cyanohydrin and an amine in water. Thus formaldehyde cyanohydrin and P-hydroxyethylamine lead to A/- (P-hydroxyethyl)hydroxyacetamide (4). 

Monoethanolamine (MEA), ethanolamine (ETA) 2-aminoethanol 2-hydroxyethylamine Nt CPLjCHjOH. MW = 61.1. Sp. gr. = 1.012. Flash point 93 °C. Also used as an absorbent for acidic gases in petrochemical operations. A breakdown product of morpholine and so is often found in secondary steam cycles systems. Thought to be superior to morpholine. Available as a 99+% alkylamine, commodity product, from several international manufacturers, including BP Chemicals PLC, Union Carbide, and Texaco Corporation. Commonly available through chemical distributors. 

Besides hydroxyethylamine-based inhibitors, 1,2-dihydroxyethylene-based inhibitors were also explored [58]. Only compoimds with the (R,R,R,R)-configuration at the four central carbon atoms demonstrated any inhibitory potency, and a hydroxyindan substituent at the terminal nitrogen atoms improved activity. Hence (2R,3R,4R,5R)-2,5-bis[(prop-2-en-l-yl)oxy]-3,4-dihydroxy-N, N -bis[(lS,2R)-2-hydroxy-2,3-dihydro-lH-inden-l-yl]hexanediamide was selected for an optimization study ( ipUsmepsini = 163 nM, K =... 

Cathepsin D. The design of inhibitors of the aspartyl protease cathepsin D started from a virtual library of peptide analogs that contained the typical hydroxyethylamine isoster for the cleavable peptide bond. As the availability of starting materials would have generated a library of about 1 billion compounds, virtual screening was applied to reduce this multitude of candidate structures to a reasonable number. The backbone of a peptide... 

N,N-Diethyl-2- [methyl(cyclohexyloxy)phosphoryl]sulfanyl -N-methylethanaminium Iodide N,N-Diethyl-2-aminoethanol N,N-Diethyl-2-hydroxyethylamine N,N-Diethylethanolamine N,N-Diethyl-N-(/3-hydroxyethyl)amine N,N-Diisopropyl-(jS)-aminoethanol N,N-Diisopropyl-2-aminoethanol /V,/V-I)i isopropylamine N,N-Diisopropylaminoethanol /V,/V,-l)iisopropylcarbodiimide N,N-Diisopropylethanolamine N,N-Dimethyl-2-chloroethylamine N/N -DimethyM -bipyridinium /V,/V,-I)imethylhydrazine N,N-Dimethyl-N-(2-chloroethyl)amine /V,/Vd)irnethyl-/i-chloroethylamine /V,/V,-Methanetetrayl Biscyclohexanamine /V./V -Thiod i-2,1 -ethanediyl Bis(N-isopropyl)-2-propanamine N,a-Dimethylphenethylam ine... 

Figure 1. Chemical structures of representative ligands investigated A) biotin, B) 2-(4 -hydroxyazobenzene) benzoic acid (HABA), C) charged (X=CH2) and neutral (X=NH2+) carboxylate MMP inhibitors, D) TIBO scaffold, E) sustiva, and F) hydroxyethylamine scaffold. The biotin derivatives," MMP inhibitors,19 TIBO analogs,21 and cathepsin D inhibitors22 derived from structures A), C), D), and F), respectively, have been published elsewhere.

Clare, R. A. Mueller, and K. Houseman, Effect of hydroxyl group configuration in hydroxyethylamine dipeptide isosteres on HIV protease inhibition Evidence for multiple binding modes, J. Med. Chem. 34 1222 (1991). 

Purification by flash column chromatography on silica (eluent petroleum ether-ethyl acetate, 2 1) gave a crystalline solid (S)-TV-(tert-butoxycarbonyl)-l-(4-methoxyphenyl)-2-hydroxyethylamine (296 mg, 74%). 

Figure 6. (a) Tetrahedral intermediate formed during aspartyl protease-catalyzed hydrolysis and (b) the( S)- and (R)-hydroxyethylamine-based isosteres. 

Asp proteases Transition state isostere Statine, hydroxyethylamine 139, 140... 

Copper(II) acetylide(reference 2), 0615 2-Hydroxyethylamine Carbon dioxide, etc., 0943 Sodium dithionite (reference 2), 4807... 

Synonyms AI3-24219 2-Aminoethanol p-Aminoethyl alcohol BRN 0505944 Caswell No. 426 CCRIS 6260 Colamine EINECS 205-483-3 EPA pesticide chemicai code 011601 P-Ethanolamine Ethylolamine Glycinol 2-Hydroxyethylamine p-Hydroxyethylamine MEA Monoethanolamine Olamine Thiofalco M-50 UN 2491 USAF EK-1597. 

Hydroxyethylamine, see Ethanolamine p-Hydroxyethylamine, see Ethanolamine 2-Hydfroxyethyl chloride, see Ethylene chlorohydrin... 

Deacetylvinblastine acylazide (62) was later shown to be an exceptionally versatile intermediate for the preparation of C-3 amides. Since nucleophilic displacement of azide occurs at relatively low temperatures under mild conditions, a wide variety of C-3 derivatives have been prepared (Scheme 1, Table III). This observation is in contrast to the direct amino-lysis of vinblastine which usually fails when the amine employed is substituted (e.g., p-hydroxyethylamine) or secondary (dimethylamine). The reactions can be conveniently followed by the disappearance of the CO—N, infrared band at 2135 cm" with the concomitant appearance of the CO—NHj band in the region 1665-1675 cm". Acetylation of the... 

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